Method of producing press-free garments and products thereof



United States Patent 3,458,869 METHOD OF PRODUCING PRESS-FREE GARMENTS AND PRODUCTS THEREOF Alex F. Gordon, Black Mountain, N.C., assignor to United Merchants and Manufacturers, Inc., New York, N.Y., a corporation of Delaware No Drawing. Filed Apr. 15, 1966, Ser. No. 542,742 Int. Cl. A41d; D06m 13/34 US. Cl. 2-243 9 Claims ABSTRACT OF THE DISCLOSURE Process for the production of press-free garments which will retain their crease, which includes the steps of impregnating the fabrics from which the garments are produced with an aqueous solution containing an aldehyde and a synergistic catalyst, the synergistic catalyst comprising an acid salt of a primary aliphatic amine and a quaternary ammonium salt of the formula:

wherein R is an aliphatic hydrocarbon group containing about twelve to about eighteen carbon atoms, Y is is an aliphatic tertiary amine or a heterocyclic tertiary amine and X is a halogen atom or mineral acid radical; and optionally an additional catalyst constituent selected from the group consisting of a salt of (1) a metal of Groups II, III or IV of the Periodic Table and (2) an organic acid, which additional constituent will impart a pH of below 7 to the aqueous solution. The impregnated fabric is then dried, out and sewn and creased as desired to form the garment and thereafter cured at an elevated temperature.

This invention relates to textile finishing procedures in general and more particularly to improved processes for the production of press-free, crease-retaining garments and the products produced thereby.

In recent years, various methods have been developed by the art for treating fabrics so as to impart durable crease characteristics to the fabrics. In the early stages of these developments, processes were discovered which resulted in the so-called wash and wear fabrics, the products thereof requiring little or no ironing to reset the crease and remove wrinkles after each washing. The standard process for transforming fabrics into wash and wear garments comprises generally initial impregnation of the fabric with a thermosetting resin, drying, and then curing the impregnated fabric by heating to effect cross linking of the resin and fibers. Thereafter, the fabric was washed, cut, sewn and pressed to result in the finished garment.

Further developments in the garment industry soon gave rise to improvements or variation over the above-defined general process resulting in the so-called permanentpress fabrics. In this later development, the fabrics were subjected to an initial impregnation with a thermosetting resin and then dried, as in the Wash and wear procedure. However, in the permanent press process, the impregnated fabric, after drying, is cut, sewn and pressed to form the completed garment, without washing and prior to curing. Thereafter the finished garment is cured by the use of heat to effect setting or cross-linking of the resin with fibers of the finished garment. This process results in the production of garments which retain their press and remain wrinkle-free even after repeated washings.

While the permanent-press technique has met with general acceptance in the garment industry, and more im- 3,458,869 Patented Aug. 5, 1969 ice portantly with consumers, a number of problems have arisen with its use which have precluded universal acceptance and satisfaction of the garments produced by the process. Foremost among these problems or difficulties is that the procedure has not been found suitable for producing garments composed entirely of cotton, particularly socalled light cottons. While some success has been attained by employing fabrics consisting of heavy cottons, i.e., eleven ounces in weight or more, no process has been developed heretofore which will effect suitable durable crease resistance in fabrics consisting of light cottons.

This problem appears to arise as a result of the thermosetting resins employed heretofore for impregnation of the fabrics as the chemicals employed have affected the tensile strength and durability of the cottons with resultant poor garment wear and discoloration. The resins primarily employed heretofore to impregnate the fabrics, and which have been found deleterious to the cotton, comprise generally the urea-formaldehyde resins, the melamine-formaldehyde resins, certain sulfones and imidazolidones. As pointed out hereinabove, none of these have yielded satisfactory results when working with all-cotton fabrics.

As cotton is one of the most desirable fabrics for garment formation, attempts have been made to circumvent the problems by employing cotton, which is composed of cellulosic fibers, fortified with synthetic fibers such as polyesters and polyamides (nylon). However, it has been found that incorporation of synthetic fibers into cotton in fact does not prevent or eliminate the deteriorative effect of the finish to the cellulosic fibers, but merely serves to mask the deterioration.

A further problem encountered by prior processes is that the extended curing cycles heretofore employed (sixteen minutes or more) have resulted in shade changes of many of the dyed fabrics. This difliculty has been particularly manifest when working with fabrics colored by dispersed dyes as the dyestuff tends to migrate from the cloth to the wall and other parts of the equipment thus resulting in difiicult cleaning and maintenance problems as well as creating shading changes and non-uniform shading. Moreover, these prior processes have not been suitable for producing white cottons by reason of the fact that white garments tend to suffer discoloration and yellowing during the curing operation and subsequent Wash and wear period. Another difiiculty connected with the problem is that the expensive equipment required to effect these long curing or setting periods has mitigated against cost reductions in carrying out the overall process. Another disadvantage resulting from the extended curing cycles of the art is that wash resistance and light fastness properties of the fabric are adversely affected by long, high temperature curing.

Still another disadvantage of processes employed heretofore is that full resin polymerization or cross-linking is not uniformly achieved as the extent and ratio of the interand intra-molecular cross-linking is not subject to effective control.

It is accordingly one object of the present invention to provide processes for producing press-free, crease-retaining garments and the products thereof which obviate the disadvantages heretofore incurred by the art.

A further object of the present invention is to provide an improved process for the production of press-free, crease-retaining garments which retain their durability and tensile strength and are not subject to color variations during production or when subjected to repeated washings during the wear period.

A still further object of the present invention is to provide an improved process for producing garments composed of cellulosic fibers by the impregnation thereof with a class of aldehydes or compounds which may release aldehydes or react as such contained in an aqueous solution wherein brief curing cycles are employed to result in cellulosic fabrics having improved tensile, tear and abrasion strength and durability.

An even further object of the present invention resides in the provision of a process for the production of pressfree, crease-retaining garments by the impregnation thereof with a resin-forming aqueous solution of aldehydes or aldehyde donor compounds containing a synergistic catalyst, wherein substantially complete resin polymerization or cross-linking is achieved with excellent control.

Other objects and advantages of the present invention will become apparent as the detailed description thereof proceeds.

In accordance with the present invention, and in satis' faction of the above objects and advantages, there is provided an improved process for the production of pressfree, crease-retaining garments which comprises impregnating the fabrics with an aqueous solution containing an aldehyde or aldehyde donor compound and a synergistic catalyst, drying the fabric, cutting and sewing to form a desired garment and then curing the garment at an elevated temperature for a short period. Also provided by the present invention are the garment products produced by the above-identified process.

When proceeding according to the process of the present invention, it has been found that press-free, crease-retaining garments may be produced which do not suffer from the disadvantages of prior garments as enumerated above. It has been found that impregnation of the fabrics with a certain aqueous solution of an aldehyde containing a synergistic catalyst results in the production of garments having a soft, lustrous hand, outstanding strength and durability properties, remain wrinkle-free and are not subject to discoloration either during the curing step or during the wash and wear period.

The novel process of the invention is considered applicable to the several types of fabrics now employed in the textile industry for forming crease-retaining garments including cellulosic and synthetic fibers in general as well as blends of these fibers, such as cotton blended with nylon or polyesters in ratios of about 40% to 60%. However, the present process is considered particularly applicable to fabrics composed solely of cellulosic fibers, sometimes called all-cottons, and this fabric forms a preferred aspect of the present invention. Even more preferred fabrics for use in the present invention are the light-cottons, or the all-cotton fabrics of less than about eleven ounces in weight. Such light cotton fabrics are eminently suitable for forming garments such as shirts, blouses, and the like, which have not been successfully commercially produced heretofore because of the processing problems enumerated hereinabove.

In carrying out the process of the invention, the selected fabrics are initially treated or impregnated with an aqueous solution containing (A) an aldehyde, aldehyde donor compounds, or a mixture of aldehydes as hereinafter defined and (B) a synergistic catalyst mixture constituted of (1) an acid salt of a primary aliphatic amine of the following formula:

R--NH -HX wherein R is an alkyl group or an aryl-alkyl group of one to about eight carbon atoms and HX is a strong acid; and (2) a quaternary ammonium salt of the following formula:

R-Y-oHlf-iR R R X wherein R is an aliphatic hydrocarbon having about twelve to about eighteen carbon atoms which can be normal or branch-chained; Y is CONH-- or -O-; and

.4 etc., and X- is a halogen anion, preferably chlorine or bromine or a mineral acid radical.

This synergistic catalyst mixture may also contain a third (3) catalyst constituent if desired, namely a salt, e.g., a halide, oxyhalide, nitrate, sulfate, etc., of a metal of. Group II, III or IV of the Periodic Table, or an organic acid, which constituent functions to impart a pH below 7 to the treating solution. Any such watersoluble metallic salt which, when added to water produced a solution having a pH below 7 may be used. Examples of such salts are the alkaline earth metals, e.g., calcium, magnesium, etc., chlorides, nitrates, bromides, chlorates and iodides; aluminum chloride or sulfate boron fluoride, soluble zinc salts including zinc silico fluoride; and zirconium oxychloride. Also, there may be employed instead of, or in conjunction with the metal salt, an organic acid such as citric acid, monochloro acetic acid, formic acid and the like with similar results.

The aldehyde reactant to be employed in the aqueous solution may be formaldehyde or any aldehyde polymer or aldehyde containing compounds which will decompose to liberate the the aldehyde radical or without decomposition will react as a free aldehyde radical under the conditions of the reaction. It has been found that any of the commercial grades of formaldehyde, glutaraldehyde, glyoxal, acrylic aldehyde (acrolein) methylacrylic aldehyde (methacrolein), and formaldehyde polymers containing not more than about six carbon atoms in the chain, which includes dialdehyde, paraformaldehyde and trioxymethylene, for example. Furthermore, amine aldehyde compounds may be employed, if desired. The aldehydecontaining compounds, such as paraformaldehyde and trioxymethylene, are considered as equivalent to formaldehyde on a weight basis and their use should be predicated on that premise. For example, two parts each of acrolein, methacrolein, glyoxal and the like are equivalent to one part formaldehyde HOCH); hence the aqueous treating solution can contain from about 2 to about 20% of acrolein, methacrolein, glyoxal, etc., on a 100% solids basis, not including solvent, with which these aldehydes are incorporated in the treating solution. If formaldehyde donors of the amine-polyaldehyde types are employed as, for example, reaction products of ureaparaformaldehyde (commercial product UF-SS of Allied Chemical Corp.) or carbamic acid esters of polyaldehyde compounds, the required amount is determined according to the actual chemical aldehyde equivalent. Further, four parts of glutaraldehyde are equivalent to one part formaldehyde and thus the treating solution can contain from 4 to 40 parts glutaraldehyde on a 100% solids basis. The remaining aldehydes listed and others considered equivalent may be employed in a similar manner.

The acid salts of the primary aliphatic amine identified generally hereinabove [component 1) of synergistic catalyst mixture (B)] include the acid salts of compounds such as monoethanol amine; butanol amine; ethylamine; 2 amino 1 butanol; Z-amino 2 methyl-l-propanol; 2-amino-2-methyl 1,3 propanediol; 2-amino-2-ethyl-1,3- propanediol, tris (hydroxy-methyl)-amino methane, etc. Thestrong acids which may be employed to form the acid salts of the above amines include the mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and organic acids such as citric acid and the like. The preferred amine salts for use in forming the aqueous solution of the invention is 2-amino-2-methyl-1- propanol hydrochloride, known commercially as Catalyst AC.

The quaternary ammonium component [component (2) above] includes such compounds as stearamide methyl pyridinium chloride, octadecyl oxymethyl pyridinium chloride, oleoyloxymethyl pyridinium chloride, stearamine methyl picolinium chloride, stearamide methyl quinolinium chloride, etc. The preferred quaternary ammonium compound for use in the solution is stearamide methyl pyridinium chloride, sold commercially under the trade name of Zelan AP, chiefly in view of the fact that it is readily available and relatively inexpensive.

The aqueous treating solution prepared employing the above-identified materials should contain from about 1% to about by weight of the aldehyde reactant (calculated as 100% HCHO), and not more than about 10% by weight of the synergistic mixture of catalysts with the catalyst components in the mixture present in approximately equal amounts. When operating with or treating cotton fabrics, a solution containing from about 1% to about 5% by weight of the aldehyde (100% HCHO) should be used. When treating rayon or viscose textiles, the aldehyde content should be from about 2% to about 10% by weight, calculated as 100% HCHO.

When using an aqueous solution containing only eatalyst components (1) and (2) above, the amount of the synergistic catalyst mixture should not exceed about 7% or 8% by weight based on the total weight of the treating solution. Preferably the solution should contain from about 0.5% to about 2% of each of the catalyst components (1) and (2) and if component (3) is also used, as preferred, it is employed in the amount of about 1.5% by weight to about 2.5% by weight of the aqueous solution.

The treating solution may also contain additives such as a small amount, for example, of from 0.1% to about 5% by weight, of a buffer to minimize degradation of cellulose fibers due to the acid catalyst. Examples of such buffers include melamine formaldehyde, triazine urea formaldehyde resins (Aerotext 23), dimethylol ethylene urea, dimethylol dihydroxy ethylene urea, or other alkylene urea derivatives. Furthermore, dicyandiamide (DCY) and the like may also be employed, if desired. The solution can also contain esters of stearylalcohol and melamine formaldehyde (Permel B sold by American Cyanamide Company) or a mixture of two or more such buffers and from about 0.5% to about 4% of glycerin, glucose or sorbitol which serves to protect the cellulose and aldehyde in the treating solution during the early stages of the processing while the aldehyde is chiefly in the liquid phase. The solution may also contain, if desired, suitable textile softeners as well as suitable deodorants.

The above aqueous solution is formed to serve as a padding or impregnating bath for the fabrics which are ultimately to be formed into garments. In a preferred embodiment, the bath employed for applying the treating solution is prepared by mixing a portion of the water with the aldehyde or aldehyde donor and the other constituents are added in solution form to the water-aldehyde mixture. The quaternary ammonium salt component is preferably added by dissolving in hot water at a temperature of about 160 F. and added to the solution. The remaining constituents, if not soluble in water at room temperature above about 70 F., are dissolved in Water at an elevated temperature below the boiling point of the water and added thusly. The temperature of the resultant bath will depend on the particular constituents employed and should be such that all constituents remain in solution. Any temperature below the boiling point of water can be used. As a practical matter, however, temperatures near room temperature or a few degrees above room temperature for example, from 70 F. to about 110 F., should be employed.

In alternative procedures for impregnating the fabrics with the treating solution, the latter may be sprayed, printed, padded or otherwise applied to impregnate the textile with the treating solution. By either treating method, however, the wet pick-up should be from about 65% to about 85% by weight based on the weight of the dry textile after extraction of the excess solution.

Before the impregnation of any of the fabrics with the aforementioned aqueous solution, it is preferable to thoroughly wash the fabrics in a suitable aqueous soap solution, including a suitable detergent to remove any starch, gelatine, glucose, dextrine, coloring matter or other impurities which may be present, and subsequently rinsing the washed fabrics in clear rinse water. This procedure is deemed necessary to avoid any undue stiffening of the material.

Following application of the treating solution to the fabric at the desired temperature and extraction of the excess solution so that the wet pickup is from about 65% to about by weight based on the dry weight of the textile, the fabric is dryed at a temperature maintained substantially below the temperature required to cure, set or polymerize the resins on the fabric. That is, the polymerization of the resin-forming ingredients of the solution, with which the fabric is impregnated, is deliberately avoided in the method of the invention during the stages of padding, stretching, finishing and drying. A preferred temperature range for drying the impregnated fabric has been found to be about 200 F. to about 260 F. for a period of from about 0.5 to about 3 minutes.

One embodiment for impregnating and drying the fabri-cs comprises winding the fabric onto rolls and then successively and continuously impregnating with the abovedescribed aqueous solution by passing the fabric through a conventional dipping or padding machine, stretching and sizing on a standard tenter frame and simultaneously dry ing as the fabric passes along the frame. Thereafter, the fabric is finally rolled onto a suitable drum for transportation to a garment makeup room where the treated fabric is cut, sewn and finished to provide the completed garment for subjection to the final curing step to effect polymerization of the resins in the garment. If desired, the fabric may be double-dipped in the abovedescribed aqueous solution to insure approximately pickup of the solution by the fabric. Extraction of excess solution may be effected by passing the impregnated fabrics through rollers operating under forced pressure so as to result in a wet pickup of about 65% to about 85 based on the dry weight of the fabric.

In the padding or impregnating step including squeezing of the fabric, approximately 65 to 85 preferably 70%, by weight of the solution is retained in the fabric as it leaves the padding machine for passage to the tenter frame for stretching and setting to size such as width. Whenever it is desired to impart a mechanical finish to the fabric, a conventional flap nip calender can be employed in conjunction with the tenter frame, the rolls of the calender being heated at the drying temperature to effect the mechanical finish. It is to be understood that the drying atmosphere of approximately 200 F. is to be maintained as the fabric is passed along the tenter frame, such drying atmosphere being substantially below the temeprature required to cure, set or polymerize the resins impregnated on the fabric.

The final roller upon which the fabric is rolled after passing through the tenter frame and fiat nip calender, if used, may or may not be heated depending upon the degree of crease resistance desired in the fabric and this is dependent upon the type of fabric being processed. It has been found that heating of this final or take-off roller usually serves to effect an increase in the crease resistance of the treated fabrics. It is preferred also to so control the drying of the solution and impregnated fabrics so as to retain approximately about 2% to about 8% of the solution or moisture content over and above the natural moisture of the fabrics. After completion of the impregnation and drying steps, the entire drum or roller with the processed or impregnated fabric, containing the residual moisture content mentioned, is then transferred to a garment preparation location for the usual steps of garment manufacturing, it being understood that the fabric, as Worked upon by the garment makers, contains the unpolymerized or unset resins in the amounts set forth hereinabove.

After the garments have been completed by the steps of cutting, sewing, and finishing, which may include pleating by a mechanical pleating step, if desired, the entire completed garments are subjected to an elevated temperature to effect complete polymerization and setting of the resin in the garments to a water-insoluble state. The curing step employed in setting or polymerizing the impregnated resins according to this invention constitutes one of the primary advantages disclosed herein as the impreg nated garments are preferably cured at a temperature of about 240 F. to about 350 F. for from about 1 to minutes, preferably about 2 to 5 minutes. For pure cottons the preferred curing temperature is about 300 F. to about 310 F. and for other textiles such as rayons and viscose textiles, the preferred curing conditions are at temperatures of about 320 F. The time required for maintaining these curing conditions to effect complete polymerization is the relatively short period of about 2 to .5 minutes, substantially below the time required in processes employed heretofore. This particularly advantageous short time curing cycle of 2 to 5 minutes represents a significant feature of the process because the shade changes of many dyed fabrics are not adversely affected thereby. Also, the short period used avoids such problems as non-uniform shading as well as shade changes in the dyed garments.

The curing operation may be carried out in a number of ways including the use of the conventional curing oven. However, a significant feature of the present process, employing the impregnant solution disclosed herein, resides in the fact that the curing operation may be carried out merely by the application of a heated press. This includes use of the well-known hot-head press, employed generally in dry-cleaning establishments to effect the pressing of garments. It is to be understood, of course, that the press is to be operated under the time and temperature conditions set out hereinabove.

The employment of a hot-head press to effect the curing step of the invention represents a decided advance over previous methods in that it eliminates the necessity for expensive garment-setting ovens employed heretofore. This feature, of course, is a significant commercial advantage as it aids in reducing the overall cost of the process.

It is to be understood, however, that the curing process of this invention, employing the aqueous solution described hereinabove, may also be carried out utilizing other heating devices including ovens known as gasfired types. If such ovens are employed, it is necessary that suitable vents be provided therein for permitting the escape of air as well as the escape of vapors emanating from the heated polymerizable resins. Also, the oven should preferably include a plurality of interiorly mounted thermocouples arranged at various locations within the oven for an accurate indication of temperature in the oven as the temperature employed in curing the garments represents a critical feature of the process.

The garments produced as a result of the process of the invention, as hereinabove described, are characterized by having a soft, silky, lustrous hand, outstanding wash resistance, durability and color retention properties and require no ironing after washing, particularly as compared with similar garments produced heretofore. It is theorized that these improvements are due to the unique synergistic catalyst system employed in accordance with the present invention and described hereinabove.

While the explanation for the improvements effected by the synergistic catalyst system is not fully known, the following explanation, believed to be correct, is given to facilitate a better understanding of the invention. It will be appreciated, however, that this invention is not to be limited to this explanation.

As applied to the treatment of cellulosic or all-cotton fibers, the synergistic catalyst system of this invention provides the most favorable conditions for the reaction between the aldehyde reactant and cellulose with substantially less deterioration of the physical properties of the cellulose than has been known heretofore. The components of the catalyst mixture of this invention are believed to cooperate to promote the reaction with optimum yield and mo none In this form, herein called the glycol form, the formaldehyde is practically non-reactive with the cellulose.

The reaction between the aldehyde and the cellulose is believed to take place for the most part during the curing step, as at the curing temperature, the aldehyde is present for split seconds in a gaseous form. Component (1) of the catalyst system provides the acidic pH simultaneously with the release of gaseous aldehyde from the glycol form at the time when the reaction takes place or at the curing temperature. The acid salt of the primary aliphatic amine [component (1)] starts to decompose and provides some hydrogen ions at temperatures lower than 200 F.; the major portion, however, does not decompose to form amine vapors and hydrogen ions until temperatures above 240 F., for example, 240 F. to about 350 F. are reached at which time the major reaction occurs.

It has further been found that the amine component reacts with the aldehyde component, i.e., formaldehyde, according to the following equation:

This methylol compound then reacts with additional formaldehyde to replace the N-hydrogen atom in the methylol group to produce compounds having the formula:

with consequent formation of a long chain oxymethylene water-soluble polymer.

From the above series of reactions, it is evident that the aldehyde in water solution and in the glycol form is fugitive and the aldehyde must be kept on the textile where it can react therewith during the curing step in order for the treatment to accomplish the desired results. The acid salt of the primary aliphatic amines is believed to serve as the chemical retainer for the aldehyde and at the same time provides the necessary acidic conditions when the amine is decomposed at the curing temperature during the curing operation to catalyze the reaction between the aldehyde and the cellulose.

The quaternary compound in the synergistic catalyst mixture is believed to promote autopolyrnerization of the aldehydes to less volatile polymerizates which are more reactive with the cellulose. The quaternary compound also exercises a desired softening effect on the garment. The presence of these quaternary compounds is particularly important during the early stages of the treatment as their presence in the treating solution or bath insure maximum utilization of the aldehyde. During the curing operation the aliphatic amine appears to exercise the more important catalytic influence in promoting the reaction between the aldehyde and cellulose and the two together therefore have a synergistic influence in terms of the overall effect on the cellulosic textiles, particularly, from the standpoint of imparting to the textiles improved durability and tensile strength properties.

The water soluble metallic salts and/or organic acids employed in the system are considered essential to promote the formation of inter-molecular cross-bonds of the celluose molecules although the intra-molecular crossbonds are less deterlorative to the cellulose than are the inter-molecular type. However, both types of cross-bonds are necessary to provide good durability, garment strength and wash and wear performance. Employing a catalyst mixture containing synergistic components (1) and (2) above and not (3), a high dry and wet crease angle can be produced with less deterioration caused by inter-molecular cross-bonds. In other words, the tensile strength is greater, and while the washing and wearing properties are good, they are not as good as is obtained when using a catalyst system containing all three components identified above. As indicated, the use of the latter system results white and dyed fabrics in the examples was to illustrate the applicability of the process of the invention to both types of materials as described in the above disclosure. The result to be achieved by use of this technique was to show that white garments produced by the process of the invention are not subject to discoloration either during the curing operation or thereafter and that the dyed cottons retain their color uniformly without suffering shade changes.

in some loss of tensile strength chiefly because of the for- 10 EXAMPLE 1 mation of more inter-molecular cross-bonds. Component Component; Percent (3) therefore, is believed responsible for more deteriora- Formaldehyde 12 tion of the physical properties of the cellulose than is Ae otex 2,0 component (1) or (2) of the synergistic catalyst mixture. Glycerine 15 Hence, a proper application of the synergistic catalyst DCY 0,25 system of this invention permits substantially complete Catalyst AC ()5 control of the extent and ratio of interand intra-molec- Calciu hl id 4,0 ular cross-links formed as the resin insolubilizes on the Z la 2 celluose fibers. This feature, in turn, makes possible the W t 77 75 control of the adverse effect of the acidic catalyst on the cellulose. Total 100 The following examples are given to illustrate the process of this invention.

In the following examples, cotton broadcloth was EXAMPLE 2 treated with the solutions set forth in the examples. The Component: Percent aqueous solution was at room temperature (70 F.) When Formaldehyde 12.0 the cloth was passed therethrough and after passage Aerotex 2.0 through the bite of the padding rollers, the fabric was left Glycerine 1.5 with a wet pick-up of about 70% based on the fabric DCY 0.25 weight. The treated cloth was then dried on the rollers at Catalyst AC 0.5 about 200 F. Zinc silicofluoride 3.0 In each of Examples 1 to 22, the aldehyde employed Zelan 2.0 Was commercial grade 37% by weight aqueous formalde- Water 78.75 hyde stabilized with methanol. The use of aqueous formaldehyde in these examples is, of course, not to be con- Total 100 sidered as limiting the class of aldehyde donors delineated hereinabove.

The Aerotex employed in the examplm was used in the EXAMPLE 3 form commercially available containing 48% solids in an Component: Percent aqueous or aqueous/isopropanol medium. The dirnethyl- Formaldehyde 12.0 olethylene urea was in the form of a water or water/iso- Aerotex 2.0 propanol solution containing 48% resin solids. The di- Glycerine 1.5 methylol-dihydroxy-ethylene urea was in the form of a DCY 0.25 aqueous solution containing 50% resin solids. The 45 Catalyst AC 0.20 Zelan was used in a concentration of 5 0% solids, the rest Zelan 2.0 being water. W r 30-25 Component (1) was Catalyst AC, but the acid salts of any other primary aliphatic amine having six or less car- Total 100 Example No 4 5 6 7 8 9 10 11 12 Formaldehyde 12. 0 12. 0 12. 0 12. 0 12. 0 12. 0 12. 0 12. 0 12. o erotex 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 2.0 Glycerin" 1. 5 1. 5 .5 1. 5 1. 5 1. 5 1. 5 1. 5 1. 5 CY 5 25 .25 5 5 5 Catalyst AC .0 0 0 0 0 an .0 .0 .0 Citric Acid Pyridinium hydrochloride Ammonium chloride.

bon atoms such as hydrochloric acid, sulfuric acid, etc. as described above, can be used with similar results. Component (2) is referred to as Zelan, the compound used being steararnide methyl pyridiniurn chloride, although other quaternary ammonium salts, as hereinabove disclosed, may be used With equal results. All percentages and values given are by weight, based on the weight of the total solution.

In each of the examples, two diiferent cotton fabrics were employed. The first consisted of plain White cotton fabrics whereas the second was cotton cloth dyed with a dispersed blue dye. The purpose of employing both plain Example No 13 14 Formaldehyde 12. 0 12. 0 Aerotex 2. 0 2. 0 Glycerin... 1. 5 1. 5 D Y 0. 25 0 25 Catalyst AC 2. 0 2. 5

7 Zelan 2. 0 2. 0 Citric acid-.. 1. 0 Formic Acid 0. 2 Water 80. 05 78.

Example No 16 17 18 19 20 21 22 Formaldehyde 5. 0 8. 0 12. 0 16. 0 4. 0 6. 0 10. 0 14. 0 Dimethylol ethylene urea 5. 6.

Dimethylol dihydroxy ethylene urea Dimethylol tetrahydro-5-hydroxy-2-pyrmndon Glycerin DCY Catalyst AC Methanol amine H Zelan Magnesium chlorid Zirconium oxychlorid Monomagnesimn phosph Pyridim'um methylene bis (iii n 1. 5 Water 15. 50

Example No 27 29 30 Acrolein g 6. 0 10. 0 l4. 0

Dimethylol ethylene urea Dimethylol dihydroxy ethylene urea. Glycerin D C Y Magnesium chloride..- Zirconium oxychloride Monomagnesium phospha Bis pyridinium methylene b Example No Glutaraldehyde Dimethylol ethylene urea Dimethylol dihydroxy ethlyene ure Glycerin DCY Catalyst A Methanol amine H01 Gibb 05 CO 0! Monomagnesium phosphate Bis pyridinium ethylene bis oxymethyl 0 W After impregnation and drying of the cotton fabrics employing the aqueous solutions set forth in the above examples, the treated fabrics were cut and sewn into sport shirts. After formation and low temperature pressing of the shirts, they were subjected to the action of a hothead press for three minutes at 310 F., during which period the setting action of the impregnated resin occurred. After removal from the press, the shirts showed a pleasing soft hand with good wear resistance and dimensional stability. The finish imparted to the garments was found to withstand repeated washings and dry cleanings and required no ironing to retain their original unwrinkled shape and creases.

The shirts produced from the white cotton fabric showed no discoloration or fading at the crease lines or anywhere on the shirts immediately following the curing operation or during the subsequent wash and wear period. The blue shirts formed from the dyed cotton fabric retained their original color uniformly throughout the curing step and wear period thus attesting to the attributes and advantages of the disclosed process.

It will be understood that other impregnating solutions of the type described hereinabove may be employed in the process of the invention with similar results obtaining. Also, the impregnated fabrics may be cut and sewn into other types of garments such as trousers, blouses and the like, as will be obvious to those skilled in the art.

It will be appreciated that this invention is not to be limited to the disclosure set forth hereinabove, but is to be limited only by the appended claims.

What is claimed is:

1. A process for the production of press-free, creaseretaining garments which comprises impregnating the fabrics from which the garments are produced with an aqueous solution containing a member selected from the group consisting of an aldehyde and a chemically equivalent aldehyde donor compound, and a synergistic catalyst, the synergistic catalyst comprising a mixture of (a) a primary aliphatic amine of the formula:

wherein R is an alkyl group having not more than about six carbon atoms and HX is a strong acid, and (b) a quaternary ammonium salt of the formula:

wherein R is an aliphatic hydrocarbon having from about twelve to about eighteen carbon atoms,

is selected from the group consisting of aliphatic tertiary amines and heterocyclic tertiary amines, and X- is selected from the group consisting of a halogen atom and a mineral acid radical, drying the impregnated fabric, cutting and sewing to form the desired garment, pressing the garment and curing the garment at an elevated temperature.

2. A process according to claim 1 wherein the fabric is composed solely of cotton.

3. A process according to claim 1 wherein the fabric is a blend of cellulosic and synthetic fibers.

4. A process according to claim 1 wherein the aqueous solution contains an additional catalyst constituent (c) selected from the group consisting of a salt of 1) a metal of Groups H, III or IV of the Periodic Table and (2) an organic acid, which constituent imparts a pH of less than about 7 to the treating solution.

5. A process according to claim 1 wherein the garments are creased during the pressing step.

6. A process according to claim 1 wherein the curing 9. Press-free, crease-retaining garments as produced by step is carried out at a temperature of about 260 F. to the process of claim 1. about 350 F. for about 2 to 5 minutes.

7. A process according to claim 1 wherein the aldehyde N0 Ieffirences Ci e and chemically equivalent aldehyde donor compounds are selected from the group consisting of formaldehyde, glutar- 5 NORMAN TORCHIN Primary Exammer aldehyde, glyoxal, acrolein, methacrolein, formaldehyde J, CANNON, Assi t t Ex mine polymers and amine-aldehyde compounds.

'8. A process according to claim 7 wherein the aldehyde US. Cl. X.R. is formaldehyde. 10 144 mg UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3 r 458 359 Dated. August 5 1969 Inventor(s) Alex F. Gordon It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

Column 1, line 21, first formula change "CH to 011 Column 1, line 27 delete "R from"NR R R R Column 6 line 44 change "flap" to flat SIGNED AND SEALED MAR 3 11970 (SEAI) Anew EdmdH-Hotdamlr.

"mm x, Ghlnal JR- 8 V Oomisaioner of Patents 

